EP0052333A1 - Dérivés du fluoro-4-oxypyrazole-5 et leur préparation - Google Patents

Dérivés du fluoro-4-oxypyrazole-5 et leur préparation Download PDF

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Publication number
EP0052333A1
EP0052333A1 EP81109602A EP81109602A EP0052333A1 EP 0052333 A1 EP0052333 A1 EP 0052333A1 EP 81109602 A EP81109602 A EP 81109602A EP 81109602 A EP81109602 A EP 81109602A EP 0052333 A1 EP0052333 A1 EP 0052333A1
Authority
EP
European Patent Office
Prior art keywords
fluoro
oxypyrazole
methyl
lower alkyl
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP81109602A
Other languages
German (de)
English (en)
Other versions
EP0052333B1 (fr
Inventor
Nobuo Ishikawa
Tomoya Kitazume
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daikin Industries Ltd
Ihara Chemical Industry Co Ltd
Original Assignee
Daikin Industries Ltd
Ihara Chemical Industry Co Ltd
Daikin Kogyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries Ltd, Ihara Chemical Industry Co Ltd, Daikin Kogyo Co Ltd filed Critical Daikin Industries Ltd
Publication of EP0052333A1 publication Critical patent/EP0052333A1/fr
Application granted granted Critical
Publication of EP0052333B1 publication Critical patent/EP0052333B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5

Definitions

  • the present invention relates to novel 4-fluoro-5-oxypyrazole derivatives which are useful as intermediates for agricultural chemicals and pharmaceutical chemicals.
  • Organic fluorine compounds have been considered to be important in view of reactivity and biological activity.
  • Futraful , 2-fluorohistidine and Diflubenzuron have been developed as pharmaceutical and agricultural chemicals.
  • the compounds having the formula (I) are novel compounds and are remarkably useful as intermediates for pharmaceutical or agricultural chemicals.
  • the typical novel 4-fluoro-5-oxypyrazole derivatives of the present invention include:
  • the 4-fluoro-5-oxypyrazole derivatives having the formula (I) can be produced by reacting methyl hydrazine or hydrazine hydrate with an ⁇ -fluoro- ⁇ -ketoester having the formula wherein R 3 represents a lower alkyl group and R 2 is defined above.
  • the reaction is advantageously performed in an alcohol while refluxing.
  • 4-Fluoro-5-oxypyrazole derivative of the present invention can be used for producing effective insecticides; 4-fluoro-pyrazole derivative having the formula (R 3 is a lower alkyl group) by reacting it with a compound having the formula

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP81109602A 1980-11-13 1981-11-10 Dérivés du fluoro-4-oxypyrazole-5 et leur préparation Expired EP0052333B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP55160136A JPS5785371A (en) 1980-11-13 1980-11-13 4-fluoro-5-oxypyrazole derivative
JP160136/80 1980-11-13

Publications (2)

Publication Number Publication Date
EP0052333A1 true EP0052333A1 (fr) 1982-05-26
EP0052333B1 EP0052333B1 (fr) 1985-05-08

Family

ID=15708644

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81109602A Expired EP0052333B1 (fr) 1980-11-13 1981-11-10 Dérivés du fluoro-4-oxypyrazole-5 et leur préparation

Country Status (4)

Country Link
US (1) US4480103A (fr)
EP (1) EP0052333B1 (fr)
JP (1) JPS5785371A (fr)
DE (1) DE3170427D1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0295233A3 (fr) * 1987-06-08 1989-03-15 Monsanto Company 3-(4-Nitrophénoxy)pyrazoles et leur utilisation comme herbicides
US4964895A (en) * 1987-06-08 1990-10-23 Monsanto Company Substituted 4-(4-nitrophenoxy) pyrazoles and their use as herbicides
US5032165A (en) * 1988-08-31 1991-07-16 Nihon Nohyaku Company, Ltd. 3-(substituted phenyl)pyrazole derivatives, salts thereof, and herbicides therefrom
EP0443059A1 (fr) * 1990-02-21 1991-08-28 Nihon Nohyaku Co., Ltd. Dérivés de 3-(phényl substitué)-pyrazol, leurs sels, leurs herbicides, et les procédés de préparation de ces dérivés ou de leurs sels
TR24287A (tr) * 1990-03-13 1991-09-01 Nihon Nohyaku Co Ltd 3-(ikameli feniluepirazol tuerevleri,bunlarin tuzla- ri,bunlardan elde edilen herb
FR2773153A1 (fr) * 1997-12-29 1999-07-02 Rhone Poulenc Agrochimie Nouveaux composes fongicides

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4575591A (en) * 1984-04-23 1986-03-11 Lugaresi Thomas J Joystick attachment for a computer keyboard
US4855442A (en) * 1988-04-13 1989-08-08 Monsanto Company Substituted 3-hydroxy pyrazoles
US6096908A (en) * 1992-01-31 2000-08-01 Kashima Oil Company Optically active fluorinated compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2829289A1 (de) * 1978-07-04 1980-01-24 Basf Ag Pyrazolaetherderivate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE785785A (fr) * 1971-07-02 1973-01-03 Bayer Ag Nouveaux esters d'acides o-pyrazolothiono-phosphoriques (phosphoniques), leur preparation et leur application comme insecticides et acaricide
DE2639258A1 (de) * 1976-09-01 1978-03-02 Bayer Ag Tert.-butyl-substituierte pyrazolyl (thiono)(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide
DE2644589A1 (de) * 1976-10-02 1978-04-06 Bayer Ag Tert.-butylsubstituierte pyrazolylcarbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2829289A1 (de) * 1978-07-04 1980-01-24 Basf Ag Pyrazolaetherderivate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN, vol. 1, no. 149, 30-11-1977 & JP - A - 52093768 (FUJI SHASHIN FILM K.K.) (06-08-1977) *
PATENT ABSTRACTS OF JAPAN, vol. 5, no. 31, 25-02-1981 & JP - A - 55 157504 (SANKYO K.K.) (08-12-1980) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0295233A3 (fr) * 1987-06-08 1989-03-15 Monsanto Company 3-(4-Nitrophénoxy)pyrazoles et leur utilisation comme herbicides
US4964895A (en) * 1987-06-08 1990-10-23 Monsanto Company Substituted 4-(4-nitrophenoxy) pyrazoles and their use as herbicides
US5032165A (en) * 1988-08-31 1991-07-16 Nihon Nohyaku Company, Ltd. 3-(substituted phenyl)pyrazole derivatives, salts thereof, and herbicides therefrom
EP0443059A1 (fr) * 1990-02-21 1991-08-28 Nihon Nohyaku Co., Ltd. Dérivés de 3-(phényl substitué)-pyrazol, leurs sels, leurs herbicides, et les procédés de préparation de ces dérivés ou de leurs sels
TR24287A (tr) * 1990-03-13 1991-09-01 Nihon Nohyaku Co Ltd 3-(ikameli feniluepirazol tuerevleri,bunlarin tuzla- ri,bunlardan elde edilen herb
FR2773153A1 (fr) * 1997-12-29 1999-07-02 Rhone Poulenc Agrochimie Nouveaux composes fongicides

Also Published As

Publication number Publication date
DE3170427D1 (en) 1985-06-13
US4480103A (en) 1984-10-30
JPS5785371A (en) 1982-05-28
EP0052333B1 (fr) 1985-05-08

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